Kyle Barker

Sales Director @ Dawn Job Board - Combining candidate video intros and resume credentials for hard and soft skill visibility up front. If you’re interested in saving top of funnel time finding talent please reach me!

Greater Toronto Area, Canada

About

Player/Coach sales leader with 15+ years of experience scaling $1M–$15M ARR across mid-market and enterprise SaaS and commercial real estate. Proven builder of high-performing SDR and AE teams across inbound, outbound, and partner-led GTM motions. Deep expertise in enterprise deal strategy, multi-stakeholder negotiations, and executive alignment, with a consistent track record of exceeding quota, shortening sales cycles, and improving forecast accuracy. MEDDIC practitioner whose teams average 110%+ quota attainment through disciplined qualification, repeatable process, and strong cross-functional collaboration. Most effective in roles that prioritize scalable GTM, partnerships, and complex buying environments over travel-intensive field coverage. Motivated by opportunities where thoughtful execution, leverage, and long-term impact matter.

Experience

  • Sales Director at Dawn - Job Search
    Apr 2026 - Present · 4 mos

    Scale your hiring capacity without adding headcount. Dawn Recruiter plugs directly into your HR function - handling posting, screening, interviews, offers, onboarding, and post-hire support so your team can move faster with less effort

  • Senior Business Development Manager at Orah
    Jan 2026 - Apr 2026 · 4 mos

    Focused on expanding market presence through strategic partnerships, executive-level engagement, and scalable go-to-market motions Work closely with education leaders to align safety, compliance, and duty-of-care initiatives with modern SaaS solutions Evaluate market fit, buyer dynamics, and execution model early in the role to ensure long-term alignment with strengths in complex, multi-stakeholder sales

  • International Workplace Group plc (Permanent Full-time · 4 yrs)
    • Senior Director Partnership Growth
      Jul 2024 - Dec 2025 · 1 yr 6 mos

      Led enterprise partnership sales across $500K - $2M ACV deals with national REITs and private investors Navigated executive, legal, finance, and operational stakeholders in complex, multi-party negotiations Reduced average partnership sales cycle 33% (9 - 6 months) by standardizing contract frameworks and approval paths Delivered 160 - 180% quota attainment (2022 - 2024) and drove 20% YoY growth in Ontario, contributing to $15M in partner-sourced ARR

    • Regional Growth Director Toronto
      Jan 2022 - Jul 2024 · 2 yrs 7 mos

      As the Director of Partnerships at Regus IWGPLC, I play a pivotal role in establishing and fostering strategic alliances, expanding business networks, and enhancing the company’s partnership portfolio across Canada. With extensive experience in the commercial real estate and global workspace solutions industry, Responsibilities include identifying high-value partnerships that support the company's mission to create flexible, innovative, and scalable work environments for businesses of all sizes.

  • National Sales Director at Modulus Data
    Jan 2017 - Jan 2022 · 5 yrs 1 mo

    Led a team of 5 AEs across enterprise and mid-market segments, managing a $6M ARR portfolio with 15% YoY growth Implemented MEDDIC across CRM and deal reviews, increasing win rates 20% and improving forecast accuracy to 85% Scaled revenue 4× to $6M+ ARR while reducing average sales cycles 30% through tighter qualification and executive alignment Grew ADP channel-sourced revenue 10×, with ADP contributing 80% of total pipeline by 2021

  • Team Lead, Enterprise Accounts, ADP at ADP
    Apr 2013 - Jan 2017 · 3 yrs 10 mos

    Led a team of 3 AEs with individual annual quotas ranging from $900K - $1.4M, consistently achieving 110%+ team attainment Coached reps through $250K - $350K ACV enterprise deals involving HR, Finance, and IT stakeholders Shortened sales cycles 20% by combining Challenger and MEDDIC playbooks